Sodium periodate → HCID 22179999, compound

HRID 1795955Notes

Reaction equation

HRID 1795955 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[C:17]([Cl:18])[N:11]2[N:10]=[C:9]1[CH:19]=CN(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:25].[Na+]>C1COCC1>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[C:17]([Cl:18])[N:11]2[N:10]=[C:9]1[CH:19]=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 86759980HCID 86759980, compound

Product 1

HCID 22179999HCID 22179999, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-benzyl-7-chloro-2-(2-dimethylamino-vinyl)-3H-pyrrolo[2,1-f][1,2,4]-triazin-4-one (1.84 g, 5.59 mmole) and sodium periodate (6.0 g, 28 mmol) in THF (70 mL) and pH 7 buffer was stirred at rt under nitrogen for 45 min. The reaction mixture was filtered through Celite®, the filtrate was extracted with EtOAc (2×80 mL). The EtOAc solution was dried over MgSO4. Concentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1.5:8.5 to 4:1) gave the title compound as a white solid (1.36 g, 84%): 1H NMR (CDCl3) δ 9.48 (s, 1H), 7.20 (m, 5H), 7.10 (d, 1H, J=4.4 Hz), 6.60 (d, 1H, J=4.4 Hz), 5.68 (s, 2H); MS (ESI+) 288.08 (M++H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. extractionthe filtrate was extracted with EtOAc (2×80 mL)
  3. dry with materialThe EtOAc solution was dried over MgSO4
  4. concentrationConcentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1.5:8.5 to 4:1)

Sources & evidence

ORD record
ord-215ca760b2444217b6cd91697fc6c794
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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